Allow Me to Retort: A Black Guy's Guide to the Constitution by Elie Mystal:
Thiel’s plan, which I imagine he hatched in a lair carved into a volcano, was to attack Gawker through a series of retaliatory lawsuits. As I said, Thiel himself had no legitimate legal case against Gawker for the article that deeply angered him. But he figured other people might. With virtually unlimited funds, Thiel decided to fund lawsuit after lawsuit against the publication. He told the New York Times that he spent nearly $10 million in supporting lawsuits against Gawker, chump change when you are as wealthy as Peter Thiel.
It's important to understand that Thiel didn’t think any particular lawsuit would succeed in bring down the site. Winning the lawsuits wasn’t actually the goal. The goal was to drain Gawker of funds by having to fight these lawsuits. Most media companies have insurance policies they take out to cover the expenses of fighting off the occasional defamation lawsuit. We live in a litigious society, and getting sued from time to time is just part of the cost of being in the media business in late-republic America. But these policies are expensive; they typically have significant deductibles, and the premiums go up the more times your company is sued. Even if a company is undefeated in court, it has to spend a lot of resources fighting off lawsuits.